This invention relates to quinoline and naphthyridine prodrugs having a 3-carboxaldehyde group, to antibacterial compositions containing said prodrugs and to a method of treating bacterial infections by administering said prodrugs.
Antibacterial compounds derived from quinolines and naphthyridines are described in the prior art. U.S. Pat. No. 4,861,779, which is incorporated herein by reference, discloses such compounds having a 3-carboxylic acid group.
European patent publication 365 943 refers to antibacterial quinoline prodrugs which have a carboxaldehyde group at the three position. Kondo et al., J. of Medicinal Chem., 31,221 (1988) refers to oral administration of 3-carboxaldehyde quinolines which are rapidly metabolized into the corresponding 3-carboxyl quinolines and result in higher serum levels than those of the corresponding 3-carboxy quinoline. Chu et al., Drugs Exptl. Clin. Res., XVI(9), 435 (1990) refers to the 3-carboxaldehyde prodrug of tosulfloxacin having improved water solubility when compared to tosulloxacin itself allowing for the development of intravenous formulations of the prodrug. These publications do not refer to tissue damage encountered with intramuscular injection of 3-carboxy quinolines.